Dichloromethane → HCID 71283739, compound

HRID 1752430Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[OH:15])[CH:5]=[CH:4][N:3]=1.[NH2:16][C:17](=[O:31])[C@@H:18]([NH:20][C:21]1[N:26]=[C:25](Cl)[N:24]=[C:23]([C:28]([NH2:30])=[O:29])[CH:22]=1)[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+].ClCCl>CN(C=O)C.[Cu]I.C(Cl)Cl.CO>[NH2:16][C:17](=[O:31])[C@@H:18]([NH:20][C:21]1[N:26]=[C:25]([O:15][C:9]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)[N:24]=[C:23]([C:28]([NH2:30])=[O:29])[CH:22]=1)[CH3:19]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-(2-aminopyridin-4-yl)-4-chlorophenol (110 mg, 0.5 mmol), (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (122 mg, 0.5 mmol), CuI (10 mg, 0.05 mmol) and Cs2CO3 (191 mg, 0.5 mmol) in DMF (3 mL) was stirred at 120° C. for 4 hrs. The reaction mixture was cooled to room temperature, worked up with dichloromethane and subjected to flash chromatography (DCM/methanol) to give (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(2-(2-aminopyridin-4-yl)-4-chlorophenoxy)pyrimidine-4-carboxamide as a white solid (189 mg, yield 85%). 1H NMR (CD3OD): 7.82-8.05 (1H, br), 7.6 (2H, m), 7.40 (2H, m), 6.80 (1H, m), 6.60 (2H, m), 4.23-4.10 (1H, m), 1.35 (3′-1, d, J=7.0 Hz). LC/MS: m/z=428 [M+H]+.

Workup

temperatureThe reaction mixture was cooled to room temperature

Sources & evidence

ORD record: ord-a2c8d90af7f1460c91dd475fa96c0cc7
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163008B2

Reaction notes

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